Hydrazine, [3-(trifluoromethyl)phenyl]-, hydrochloride (1:1)

Off-white powder

General procedure: CuBr (36 mg, 0.25 mmol, 2.5 mol percent), L3 (110 mg, 0.4 mmol, 4 mol percent), H2O (0.5 mL), and K3PO4 (254 mg, 1.2 mmol) were mixedin a 15 mL screw cap test tube. After STAC (110 mg, 0.3 mmol, 3 mol percent) and aryl bromide (10 mmol) were added, the resulting mixture was stirred at 80-110° C (bath temperature) for 10 min.Then K3PO4 (2.29 g, 10.8 mmol) and N2H4*H2O (1 g, 20 mmol) were added and argon (flow rate 5-7 mL/min) was bubbled through thereaction mixture for 5 min.28 The reaction mixture was stirred ina closed test tube at 80-110° C (bath temperature) for 1-2 h until complete consumption of starting material was observed as monitoredby TLC (eluentehexane), then cooled to room temperatureand diluted with SH2Cl2 (50 mL). The resulting solutionwas filteredand washed with brine (225 mL). Aq HCl (37percent) was added to the CH2Cl2 solution dropwise until pH 3-4. The formed precipitate was filtered, washed with SH2Cl2 (15 mL) and dried atroom temperature. NMR spectra of certain synthesized aryl hydrazine hydrochlorides showed that they contained 1-5 mol percent of the corresponding aniline hydrochlorides as impurities (see Supplementary data). Analytical samples of aryl hydrazine hydrochlorides were purified via precipitation from methanol solution by adding 2-3 volumes of diethyl ether.General procedure: The pyrazolo[4, 3-c]pyridin-4-one derivatives were synthesizedby using compound 15 as starting material in two steps. Infirst step, the compound 15 (1 mmol, 137 mg) was dissolved inethanol (20 mL) and substituted phenylhydrazine hydrochloride(1.1 equivalent) was added. The reaction mixture was stirred atroom temperature for 2 h. The completion of reaction was monitoredby TLC. The resulted reaction mixture was allowed to cool toroom temperature. The solvent was evaporated under vacuum; ethanol (5 mL) was added and sonicated for 30 s to produce suspension.The resulted suspensions were kept in refrigerator for 1 hto settle down the suspended particles. The suspended particleswas filtered out and used for second step without further purification.In second step, the resulted solid was poured in boilingnitrobenzene at 210 C and stirred at same temperature for 15 min[27]. The completion of reaction was monitored by TLC. After thecompletion, the reaction mixture was allowed to cool to roomtemperature followed by silica gel column chromatography toisolate pure pyrazolo[4, 3ec]pyridine4eone derivatives (12a-12p).

Molecular Weight:212.60
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:1
Exact Mass:212.0328104
Monoisotopic Mass:212.0328104
Topological Polar Surface Area:38
Heavy Atom Count:13
Complexity:146
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes